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Old 07-18-2022, 05:02 PM   #1
ADR58
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Emailing fails - calibre 6.1 and Yahoo

I'm struggling to get 'Sharing books by Email' to work in calibre and would appreciate some assistance.

I get the following log with a test email using Yahoo...

Traceback (most recent call last):
File "calibre\gui2\wizard\send_email.py", line 223, in test_email_settings
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 739, in login
File "smtplib.py", line 642, in auth
File "smtplib.py", line 432, in docmd
File "smtplib.py", line 405, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed


Log:
connect: ('smtp.mail.yahoo.com', 465)
connect: to ('smtp.mail.yahoo.com', 465) None
reply: b'220 smtp.mail.yahoo.com ESMTP ready\r\n'
reply: retcode (220); Msg: b'smtp.mail.yahoo.com ESMTP ready'
connect: b'smtp.mail.yahoo.com ESMTP ready'
send: 'ehlo [10.152.0.6]\r\n'
reply: b'250-hermes--production-gq1-56bb98dbc7-fxknz Hello [10.152.0.6] [136.144.19.243])\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-SIZE 41697280\r\n'
reply: b'250 AUTH PLAIN LOGIN XOAUTH2 OAUTHBEARER\r\n'
reply: retcode (250); Msg: b'hermes--production-gq1-56bb98dbc7-fxknz Hello [10.152.0.6] [136.144.19.243])\nPIPELINING\nENHANCEDSTATUSCODES\n8BITMIME\nSIZE 41697280\nAUTH PLAIN LOGIN XOAUTH2 OAUTHBEARER'
send: AUTH <censored>
reply: b'535 5.7.0 (#AUTH005) Too many bad auth attempts.\r\n'
reply: retcode (535); Msg: b'5.7.0 (#AUTH005) Too many bad auth attempts.'
send: AUTH <censored>
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Old 07-18-2022, 05:08 PM   #2
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Quote:
send: AUTH <censored>
reply: b'535 5.7.0 (#AUTH005) Too many bad auth attempts.\r\n'
reply: retcode (535); Msg: b'5.7.0 #AUTH005) Too many bad auth attempts.'
send: AUTH <censored>
It appears that either the user name or the password you are using for your Yahoo account are incorrect. Alternatively, Yahoo is not allowing SMTP connections for your user and you will need to enable SMTP in your account settings.

Last edited by DNSB; 07-18-2022 at 05:10 PM.
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Old 07-18-2022, 06:28 PM   #3
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Originally Posted by DNSB View Post
It appears that either the user name or the password you are using for your Yahoo account are incorrect. Alternatively, Yahoo is not allowing SMTP connections for your user and you will need to enable SMTP in your account settings.
UN and PW are good and i can send and receive emails via Yahoo. Just not via calibre

GMX doesn't let me create an email account. All I get when submitting is...

[X] CLOSE
The requested URL was rejected. Please consult with your administrator.

Your support ID is: <17031799125825785136>

[Go Back]
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Old 07-18-2022, 06:31 PM   #4
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Quote:
Originally Posted by ADR58 View Post
UN and PW are good and i can send and receive emails via Yahoo. Just not via calibre

GMX doesn't let me create an email account. All I get when submitting is...

[X] CLOSE
The requested URL was rejected. Please consult with your administrator.

Your support ID is: <17031799125825785136>

[Go Back]
Try GMail or Outlook.
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Old 07-18-2022, 06:44 PM   #5
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Originally Posted by JSWolf View Post
Try GMail or Outlook.
Gmail SMTP doesn't work anymore as stated by calibre. Google has stopped less secure app access after May 22.

I did just go ahead and create a unique Outlook address, just for calibre, and that now seems to be working.

Still don't understand the issue with Yahoo though.
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Old 07-18-2022, 06:48 PM   #6
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Quote:
Originally Posted by ADR58 View Post
Still don't understand the issue with Yahoo though.
Did you enable Less Secure Apps for your Yahoo email account? Another possibility is that Yahoo only supports ports 465 for SSL connections or 587 for TLS connections so you would need to select the correct radio button in the Share by email preferences.
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Old 07-18-2022, 09:44 PM   #7
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gmail will work if you enable two factor auth and setup an app password and use that in calibre. No clue what hoops you have to jump through for yahoo.
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